(2-Trifluoromethyl-pyridin-3-yl)-methanol Chemical Properties

Boiling point:

209℃

Density 

1.362

Flash point:

80℃

storage temp. 

Sealed in dry,Room Temperature

pka

13.08±0.10(Predicted)

Appearance

Light yellow to yellow Solid

Safety Information

HS Code 

2933399990

(2-Trifluoromethyl-pyridin-3-yl)-methanol Usage And Synthesis

Synthesis

General procedure for the synthesis of (2-trifluoromethyl-pyridin-3-yl)-methanol from ethyl 2-trifluoromethylnicotinate: sodium borohydride (0.35 g, 9.1 mmol) was suspended in anhydrous tetrahydrofuran (20 mL). Anhydrous tetrahydrofuran solution (20 mL) of ethyl 2-trifluoromethylnicotinate (1.00 g, 0.46 mmol) was added dropwise to the stirred suspension under ice bath cooling. The reaction mixture was stirred at 4°C for 16 hours. Upon completion of the reaction, methanol (5 mL) was added to quench the residual sodium borohydride, followed by the addition of 15% aqueous sodium hydroxide solution (25 mL). The resulting mixture was continued to be stirred at 25 °C for 30 min, followed by removal of tetrahydrofuran and methanol by rotary evaporation. The remaining aqueous phase was extracted with ethyl acetate (3 x 25 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to afford the target product (2-trifluoromethyl-pyridin-3-yl)-methanol as a yellow oil (0.61 g, 75% yield), which could be used in subsequent reactions without further purification. The product was characterized by 1H-NMR (CDCl3): δ 8.64 (d, J = 4.5 Hz, 1H), 8.17 (d, J = 8.0 Hz, 1H), 7.57 (dd, J = 8.0, 4.5 Hz, 1H), 4.98 (s, 2H), 1.99 (s, 1H). Mass spectrum (ESI+): m/z (M + H)+ = 178.

References

[1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 5352 - 5359
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2146 - 2163
[3] Synthesis, 2005, # 16, p. 2751 - 2757
[4] Patent: WO2015/187934, 2015, A1. Location in patent: Paragraph 0228

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